HCID 1622515, compound → 9-Methoxy-3,4-dihydro-1-benzoxepin-5(2H)-one

HRID 917485Notes

Reaction equation

HRID 917485 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][CH:13]=[CH:12][C:4]=1[O:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]2[O:5][CH2:6][CH2:7][CH2:8][C:9](=[O:11])[C:12]=2[CH:13]=[CH:14][CH:15]=1

Participants

3

Reactant 1

HCID 1622515HCID 1622515, compound

Product 1

HCID 146616269-Methoxy-3,4-dihydro-1-benzoxepin-5(2H)-oneYield 10%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To PPA in toluene at 100° C., was added 4-(2-methoxyphenoxy)butanoic acid and the mixture stirred overnight. The mixture was poured onto ice-water, and extracted with ether (3 times). The combined organic phase was washed with water and dried over anhydrous sodium sulfate. Evaporation of the organic phase afforded a light yellow oil in 10% yield: 1H NMR δ 7.33 (dd, 1H, J=4.4, 5.1 Hz), 7.03 (d, 2H, J=4.3 Hz), 4.31 (t, 2H, J=6.6 Hz), 3.90 (s, 3H), 2.90 (t, 2H, J=6.9 Hz), 2.22 (p, 2H, J=6.8 Hz).

Workup

  1. additionThe mixture was poured onto ice-water
  2. extractionextracted with ether (3 times)
  3. washThe combined organic phase was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the organic phase
  6. customafforded a light yellow oil in 10% yield

Sources & evidence

ORD record
ord-238d72cbe2484c3ea6fcbe340760ebb5
Source dataset
uspto-grants-2007_09
Patent number
US07273880B2

Reaction notes

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